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Synthesis of γ-(Arylamino)butyric Acid Derivatives via Ring-Opening Addition of Arylamines to Cyclopropane-1,1-Dicarboxylates

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Abstract

A rapid and efficient catalytic approach has been proposed for the synthesis of dimethyl 2-[2-(aryl-amino)but-3-en-1-yl]- and 2-[2-(arylamino)-2-phenylethyl]malonates in good yields (49-95%) by ring-opening reaction of dimethyl 2-vinyl- and 2-phenylcyclopropane-1,1-dicarboxylates with arylamines in the presence of Yb(III) catalyst under microwave irradiation. The synthesized compounds are convenient precursors to γ-(aryl-amino)butyric acid derivatives.

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References

  1. Macdonald, R.L. and Olsen, R.W., Annu. Rev. Neurosci., 1994, 17, p. 569. doi 10.1146/annurev.ne.17.030194.003033

    Article  CAS  Google Scholar 

  2. Sieghart, W., Pharmacol. Rev., 1995, 47, p. 181. doi 10.1016/1043-6618(95)80095-6

    CAS  PubMed  Google Scholar 

  3. Farrant, M. and Zoltan, N., Nat. Rev. Neurosci., 2005, 6, p. 215. doi 10.1038/nrn1625

    Article  CAS  Google Scholar 

  4. Sigel, E. and Steinmann, M.E., J. Biol. Chem., 2012, 287, p. 40224. doi 10.1074/jbc.R112.386664

    Article  CAS  Google Scholar 

  5. Yogeeswari, P., Ragahendran, J.V., and Sriram, D., Recent Pat. CNS Drug Discovery, 2006, 1, p. 113

    Article  CAS  Google Scholar 

  6. Andersen, K.E., Sørensen, J.L., Lau, J., Lundt, B.F., Petersen, H., Huusfeldt, P.O., Suzdak, P.D., and Swedber, M.D.B., J. Med. Chem., 2001, 44, p. 2152. doi 10.1021/jm990513k

    Article  CAS  Google Scholar 

  7. Ma, J., Lin, J., Zhao, L., Harms, K., Marsch, M., Xie, X., and Meggers, E., Angew. Chem., Int. Ed., 2018, 57, p. 11193. doi 10.1002/anie.201804040

    Article  CAS  Google Scholar 

  8. Reznikov, A.N., Golovin, E.V., and Klimochkin, Y.N., Russ. J. Org. Chem., 2013, 49, p. 663. doi 10.1134/S107042801411027X

    Article  CAS  Google Scholar 

  9. Liu, H., Yuan, J., Tian, Q., Ji, N., and He, W., J. Mater. Sci. Chem. Eng., 2017, 5, p. 25.

    CAS  Google Scholar 

  10. Dryanska, V. and Pashkuleva, I., Org. Prep. Proced. Int., 1999, 31, p. 232. doi 10.1080/ 00304949909355722

    Article  CAS  Google Scholar 

  11. Ramachandran, P.V., Mitsuhashi, W., and Biswas, B., Org. Chem. Front., 2015, 2, p. 885. doi 10.1039/C5QO00133A

    Article  CAS  Google Scholar 

  12. Nair, V., Varghese, V., Babu, B.P., Sinu, C.R., and Suresh, E., Org. Biomol. Chem., 2010, 8, p. 761. doi 10.1039/b922981g

    Article  CAS  Google Scholar 

  13. Castillo, M.D.D., Corzo, N., González, L., and Olano, A., J. Agric. Food Chem., 1999, 47, p. 4137. doi 10.1021/jf990150x

    Article  Google Scholar 

  14. Usifoh, C.O., Lambert, D.M., Wouters, J., and Scriba, G.K.E., Arch. Pharm. (Weinheim), 2001, 334, p. 323. doi 10.1002/1521-4184(200110) 334:10<323::aid-ardp323>3.0.co;2-o

    Article  CAS  Google Scholar 

  15. Blanchard, L.A. and Schneider, J.A., J. Org. Chem., 1986, 51, p. 1372. doi 10.1021/jo00358a045

    Article  CAS  Google Scholar 

  16. Zhou, Y.Y., Wang, L.J., Li, J., Sun, X.L., and Tang, Y., J. Am. Chem. Soc., 2012, 134, p. 9066. 10.1021/ ja302691r

    Article  CAS  Google Scholar 

  17. Xia, Y., Lin, L., Chang, F., Liao, Y., Liu, X., and Feng, X., Angew. Chem., Int. Ed., 2016, 55, p. 12228. doi 10.1002/anie.201604735.

    Article  CAS  Google Scholar 

  18. Danishefsky, S., Acc. Chem. Res., 1979, 12, p. 66. doi 10.1021/ar50134a004

    Article  CAS  Google Scholar 

  19. Wong, H.N.C., Hon, M.Y., Tse, C.W., Yip, Y.C., Tanko, J., and Hudlicky, T., Chem. Rev., 1989, 89, p. 165. doi 10.1021/cr00091a005

    Article  CAS  Google Scholar 

  20. Yu, M. and Pagenkopf, B.L., Tetrahedron, 2005, 61, p. 321. doi 10.1016/j.tet.2004.10.077

    Article  CAS  Google Scholar 

  21. Uddin, M.I., Mimoto, A., Nakano, K., Ichikawa, Y., and Kotsuki, H., Tetrahedron. Lett., 2008, 49. p 5867. doi 10.1016/j.tetlet.2008.07.142

  22. Dey, R. and Banerjee, P., Org. Lett., 2017, 19, p. 304. doi 10.1021/acs.orglett.6b03276

    Article  CAS  Google Scholar 

  23. Novikov, R.A., Tarasova, A.V., Korolev, V.A., Timofeev, V.P., and Tomilov, Yu.V., Angew. Chem., 2014, 126, p. 3251. doi 10.1002/ange.201306186

    Article  Google Scholar 

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Correspondence to L. L. Huang.

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Li, S.K., Huang, L.L., Lv, Y.D. et al. Synthesis of γ-(Arylamino)butyric Acid Derivatives via Ring-Opening Addition of Arylamines to Cyclopropane-1,1-Dicarboxylates. Russ J Org Chem 55, 1432–1438 (2019). https://doi.org/10.1134/S1070428019090252

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